Water → HCID 67150313, compound

HRID 1024480Notes

Reaction equation

HRID 1024480 reaction equation
[CH3:1][CH:2]([CH3:25])[CH:3]([NH:8][C:9]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)=[CH:14][N:15]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1.O>CC(C)=O>[F:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][NH:22][C:19]2[CH:20]=[CH:21][C:16]([C:13]3[S:12][C:11]([C:9]([NH:8][CH:3]([CH:2]([CH3:25])[CH3:1])[C:4]([O:6][CH3:7])=[O:5])=[O:10])=[N:15][CH:14]=3)=[CH:17][CH:18]=2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 67150324Methyl 3-methyl-2-(5-(4-nitrophenyl)thiazole-2-carboxamido)butanoate2×

Product 1

HCID 67150313HCID 67150313, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
62.5 °C

Procedure

To a solution of the methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate (Intermediate 2, 250 mg) in acetone (8 ml) was added potassium carbonate (155 mg, 1.5 eq) and 1-(bromomethyl)-4-fluorobenzene (0.112 ml, 1.2 eq). The reaction mixture was stirred for 8 hours at 60-65° C. Water was added after the completion of the reaction, and the reaction mixture was extracted with ethyl acetate. Organic layer was washed with water and concentrated. The compound was purified by column chromatography using 10-15% ethylacetate in petroleum ether to give the title compound. Yield: 130 mg (39%). 1H NMR (CDCl3; 300 MHz): δ 7.87 (s, 1H), 7.66 (d, 1H), 7.44 (d, 2H), 7.37 (m, 2H), 7.08 (t, 2H), 6.68 (d, 2H), 4.74 (m, 1H), 4.37 (s, 2H), 3.79 (s, 3H), 2.37 (m, 1H), 1.05 (t, 6H); MS (ESI) m/z 442.1 [M+H]+, 464.1 [M+Na]+.

Workup

  1. customafter the completion of the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washOrganic layer was washed with water
  4. concentrationconcentrated
  5. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-8a9441b547d3415ab80c0c188af89889
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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